originally posted Tuesday, May 27, 2008
Some Like It Hot: One of the all-time funniest movies. Jack Lemmon, Tony Curtis and Marilyn Monroe are all at the top of their game. Jack Lemmon gives what may be the greatest comic performance in cinema. And to top it off ... you also get the great Joe E. Brown in single-minded pursuit after the cross-dressing Jack Lemmon.
Tootsie: A close second to Some Like It Hot. Dustin Hoffman, Bill Murray, Terri Garr, and Jessica Lange are all phenomenal. And kudos to the late director Sidney Pollack for his great cameo as Hoffman's exasperated agent.
Victor/Victoria: In 1930s Paris Julie Andrews plays a struggling female singer who cannot get a job. Her friend (played by the fabulous Robert Preston) comes up with a scheme: Victoria will pretend to be a man pretending to be a woman and get a job as a female impersonator in a nightclub. Then Chicago mobster James Garner finds himself oddly attracted to "Victor". Great, great movie.
Psycho: What else do you need to know? Anthony Perkins as a cross-dressing murderer masquerading as Mama.
Dressed To Kill: Michael Caine is chilling as a cross-dressing psychopath.
The Crying Game: Infamous movie about a member of the Irish Republican Army (IRA) who executes one of his hostages and then goes on to have a relationship with the murdered man's girlfriend.
Nuns on the Run: Comic silliness with Eric Idle and Robbie Coltrane as criminals who hide out in a convent dressed as nuns.
To Wong Foo, Thanks for Everything! Julie Newmar: Hilarious movie with Patrick Swazye and Wesley Snipes as transvestites who get marooned in a small town and get involved with the locals and their troubles.
Ed Wood: Directed by Tim Burton (in glorous black and white) and starring Johnny Depp as the cross-dressing cult movie maker, and all around weirdo, Edward D. Wood, Jr. The film concerns the period in Wood's life when he made his best-known films and also his relationship with actor Bela Lugosi, played with magical intensity by Martin Landau.
WORSE CROSS-DRESSING MOVIES
Glen or Glenda: Usually considered one of the worst movies ever made, it has become a cult classic due to its awfulness. Directed and starring Ed Wood (with a drug-addicted and impoverished Bela Lugosi) with such ineptness it inspired a movie that was 100 times better, Ed Wood.
Mrs. Doubtfire: Robin Williams in drag so he can see his kids ... it's even worse than it sounds, mainly because it is directed by the vapid Chris Columbus.
Yentl: Barbra Streisand cross-dresses as a Jewish man so she can study law. Bad, bad, bad ...